2-METHOXYESTRONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H24O3
Molecular Weight	300.3921
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(O)C=C2CC[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@@H]3C2=C1

InChI

InChIKey=WHEUWNKSCXYKBU-QPWUGHHJSA-N

InChI=1S/C19H24O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-16(20)17(22-2)10-14(11)12/h9-10,12-13,15,20H,3-8H2,1-2H3/t12-,13+,15-,19-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C19H24O3
Molecular Weight	300.3921
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
Profiling oestrogens and testosterone in human urine by stable isotope dilution/benchtop gas chromatography-mass spectrometry.	2010-12-12	20619283
Estrogens and development of pulmonary hypertension: interaction of estradiol metabolism and pulmonary vascular disease.	2010-12	20881610
Comparison of estrogens and estrogen metabolites in human breast tissue and urine.	2010-08-02	20678202
The normal breast microenvironment of premenopausal women differentially influences the behavior of breast cancer cells in vitro and in vivo.	2010-05-21	20492690
The coordinated p53 and estrogen receptor cis-regulation at an FLT1 promoter SNP is specific to genotoxic stress and estrogenic compound.	2010-04-21	20422012
Simultaneous determination of eight estrogens and their metabolites in serum using liquid chromatography with electrochemical detection.	2010-04-15	20188920
Activity of 2 methoxyestradiol (Panzem NCD) in advanced, platinum-resistant ovarian cancer and primary peritoneal carcinomatosis: a Hoosier Oncology Group trial.	2009-10	19577796
The in vivo properties of STX243: a potent angiogenesis inhibitor in breast cancer.	2008-11-04	18841154
The therapeutic potential of a series of orally bioavailable anti-angiogenic microtubule disruptors as therapy for hormone-independent prostate and breast cancers.	2007-12-17	18026194
Evaluation of electrospray ionization and atmospheric pressure chemical ionization for simultaneous detection of estrone and its metabolites using high-performance liquid chromatography/tandem mass spectrometry.	2007-12-01	17988961
HPLC for stress-free screening of potential prostate cancer marker catechol estrogens in urine using a diamond-electrode electrochemical and a fluorescence detector.	2007-09	17668912
Effects of a catechol-O-methyltransferase inhibitor on catechol estrogen-induced cellular transformation, chromosome aberrations and apoptosis in Syrian hamster embryo cells.	2007-04-15	17230533
Estrogen metabolism modulates bone density in men.	2007-04	17406768
Urinary phytoestrogen excretion of rats bearing methylnitrosourea-induced mammary carcinoma in response to treatment with 2-methoxyestradiol.	2007-02	17081745
Phase I safety, pharmacokinetic and pharmacodynamic studies of 2-methoxyestradiol alone or in combination with docetaxel in patients with locally recurrent or metastatic breast cancer.	2007-02	16969706
Effects of dioxin on metabolism of estrogens in waste incinerator workers.	2007-01-12	17214292
2-methoxyestradiol inhibits differentiation and is cytotoxic to osteoclasts.	2006-10-01	16619269
Plasma protein binding of the investigational anticancer agent 2-methoxyestradiol.	2006-09	16940808
The Association of the COMT V158M Polymorphism with Endometrial/Ovarian Cancer in HNPCC Families Adhering to the Amsterdam Criteria.	2006-05-15	20223014
Analysis of fifteen estrogen metabolites using packed column supercritical fluid chromatography-mass spectrometry.	2006-03-01	16503607
The role of 17beta-hydroxysteroid dehydrogenases in modulating the activity of 2-methoxyestradiol in breast cancer cells.	2006-01-01	16397246
A phase II multicenter, randomized, double-blind, safety trial assessing the pharmacokinetics, pharmacodynamics, and efficacy of oral 2-methoxyestradiol capsules in hormone-refractory prostate cancer.	2005-09-15	16166441
Selective insensitivity of ZR-75-1 human breast cancer cells to 2-methoxyestradiol: evidence for type II 17beta-hydroxysteroid dehydrogenase as the underlying cause.	2005-07-01	15994956
The oxidative metabolism of estrogen modulates response to ERT/HRT in postmenopausal women.	2004-09	15336604
Inhibition of in vitro angiogenesis by 2-methoxy- and 2-ethyl-estrogen sulfamates.	2004-04-20	14991574
Pharmacokinetics and efficacy of 2-methoxyoestradiol and 2-methoxyoestradiol-bis-sulphamate in vivo in rodents.	2004-02-23	14970876
Recent translational research: antiangiogenic therapy for breast cancer - where do we stand?	2004	15084233
Comparison of ex vivo inhibitory effect between 2-hydroxyestradiol and its 17-sulfate on rat hepatic microsomal lipid peroxidation.	2003-08	14577664
The effects of 2-substituted oestrogen sulphamates on the growth of prostate and ovarian cancer cells.	2003-02	12711018
Evaluation of an EIA method for measuring serum levels of the estrogen metabolite 2-hydroxyestrone in adults.	2001-01	11090660
Involvement of genotoxic effects in the initiation of estrogen-induced cellular transformation: studies using Syrian hamster embryo cells treated with 17beta-estradiol and eight of its metabolites.	2000-04-01	10728588
Inhibition of deoxyglucose uptake in MCF-7 breast cancer cells by 2-methoxyestrone and 2-methoxyestrone-3-O-sulfamate.	2000-02-25	10715539
Altered profile of endogenous steroids in the urine of patients with prolactinoma.	1998-10	9812172
Metabolism of 2-methoxyestrone in normal men.	1983-08	6863476
Radioimmunoassay of 2-hydroxyesterone and 2-methoxyestrone in human urine.	1979-05	462497

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:49:49 GMT 2025` Edited by `admin` on `Mon Mar 31 17:49:49 GMT 2025`
Record UNII	SJ5857RRL3
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GSS-33

Preferred Name

English

2-METHOXYESTRONE

Common Name

English

ESTRA-1,3,5(10)-TRIEN-17-ONE, 3-HYDROXY-2-METHOXY-

Systematic Name

English

2-METHOXY-3-HYDROXYESTRA-1,3,5(10)-TRIEN-17-ONE

Systematic Name

English

2-HYDROXYESTRONE 2-METHYL ETHER

Common Name

English

2-METHOXY-17-OXOESTRA-1,3,5(10)-TRIEN-3-OL

Systematic Name

English

ESTRONE, 2-METHOXY-

Common Name

English

3-HYDROXY-2-METHOXYESTRA-1,3,5(10)-TRIEN-17-ONE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2181